%0 Generic %A Shao, Wenjie %A L. J. Clive, Derrick %D 2015 %T A Family of Routes to Substituted Phenols, Including Meta-Substituted Phenols %U https://acs.figshare.com/articles/dataset/A_Family_of_Routes_to_Substituted_Phenols_Including_Meta_Substituted_Phenols/2097346 %R 10.1021/acs.joc.5b02187.s001 %2 https://acs.figshare.com/ndownloader/files/3730588 %K electrophile %K regiochemically %K ArSR %K sequence %K deprotonated %K compound %K meta %K sulfide %K substituent %K substitution patterns %K variety %K Substituted Phenols %K PhMe %K ArSAr %K Bromo %K Grignard reagent %K latter process %K PhenolsA %K benzene derivatives %K phenolic hydroxyl %K ArSePh %K benzenediol %K selenide %K phenolic azides %K ArN %K anion %K room temperature %K DBU %K substitution pattern %K aromatization %X A new family of routes to substituted phenols has been developed. 2-Bromo-3-methoxycyclohex-2-en-1-ones are readily deprotonated at C-6, and the resulting anions react smoothly with a variety of electrophiles; treatment with DBU in PhMe at room temperature then results in efficient aromatization to benzene derivatives of a regiochemically defined substitution pattern. This sequence affords phenolic azides (ArN3), sulfides (ArSR, ArSAr′), selenides (ArSePh), alcohols [ArCH­(OH)­R], amino derivatives [ArCH­(NHSO2Ar′)­R), and 1,2-benzenediols. A complementary set of substitution patterns is obtained by DIBAL-H reduction or reaction with a Grignard reagent before aromatization; the latter process gives compounds in which the newly introduced substituent is meta to the phenolic hydroxyl. %I ACS Publications